Synthesis of hexahydro-1 H-isoindole derivatives from arylacyl bromides via homoallenic bromohydrins

Mei Huey Lin, Yi Syuan Li, Chung Kai Kuo, Chung Hao Chen, Yen Chih Huang, Kung Yu Liang, Yu Chun Chen, Chang Hsien Tsai, Tsung Hsun Chuang

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

A procedure has been developed for the concise synthesis of hexahydro-1H-isoindole derivatives starting from phenacyl bromides. The approach employs a sequence involving an initial indium-mediated allenylation reaction of an arylacyl bromide with propargyl bromide. This process is followed by FeBr3-mediated SN2′-type substitution reaction of the formed homoallenic bromohydrin to produce a 2,5-dibromo-4-aryl-1,3-pentadiene, which then is subjected to a sequential, one-pot N-alkylation reaction with N-allyl-N-(p-tosyl)amine and a highly diastereoselective intramolecular Diels-Alder reaction of the formed ene-diene to generate the target hexahydro-1H-isoindole.

Original languageEnglish
Pages (from-to)2462-2466
Number of pages5
JournalJournal of Organic Chemistry
Volume80
Issue number4
DOIs
Publication statusPublished - 2015 Feb 20

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Isoindoles
Bromides
Derivatives
Indium
Alkylation
Amines
Substitution reactions
bromohydrins

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Cite this

Lin, Mei Huey ; Li, Yi Syuan ; Kuo, Chung Kai ; Chen, Chung Hao ; Huang, Yen Chih ; Liang, Kung Yu ; Chen, Yu Chun ; Tsai, Chang Hsien ; Chuang, Tsung Hsun. / Synthesis of hexahydro-1 H-isoindole derivatives from arylacyl bromides via homoallenic bromohydrins. In: Journal of Organic Chemistry. 2015 ; Vol. 80, No. 4. pp. 2462-2466.
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abstract = "A procedure has been developed for the concise synthesis of hexahydro-1H-isoindole derivatives starting from phenacyl bromides. The approach employs a sequence involving an initial indium-mediated allenylation reaction of an arylacyl bromide with propargyl bromide. This process is followed by FeBr3-mediated SN2′-type substitution reaction of the formed homoallenic bromohydrin to produce a 2,5-dibromo-4-aryl-1,3-pentadiene, which then is subjected to a sequential, one-pot N-alkylation reaction with N-allyl-N-(p-tosyl)amine and a highly diastereoselective intramolecular Diels-Alder reaction of the formed ene-diene to generate the target hexahydro-1H-isoindole.",
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Lin, MH, Li, YS, Kuo, CK, Chen, CH, Huang, YC, Liang, KY, Chen, YC, Tsai, CH & Chuang, TH 2015, 'Synthesis of hexahydro-1 H-isoindole derivatives from arylacyl bromides via homoallenic bromohydrins', Journal of Organic Chemistry, vol. 80, no. 4, pp. 2462-2466. https://doi.org/10.1021/acs.joc.5b00072

Synthesis of hexahydro-1 H-isoindole derivatives from arylacyl bromides via homoallenic bromohydrins. / Lin, Mei Huey; Li, Yi Syuan; Kuo, Chung Kai; Chen, Chung Hao; Huang, Yen Chih; Liang, Kung Yu; Chen, Yu Chun; Tsai, Chang Hsien; Chuang, Tsung Hsun.

In: Journal of Organic Chemistry, Vol. 80, No. 4, 20.02.2015, p. 2462-2466.

Research output: Contribution to journalArticle

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AU - Lin, Mei Huey

AU - Li, Yi Syuan

AU - Kuo, Chung Kai

AU - Chen, Chung Hao

AU - Huang, Yen Chih

AU - Liang, Kung Yu

AU - Chen, Yu Chun

AU - Tsai, Chang Hsien

AU - Chuang, Tsung Hsun

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